3-Bromo-5-formylbenzamide → 3-Bromo-5-formylbenzonitrile

HRID 562287Notes

Reaction equation

HRID 562287 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH:11]=[O:12])[CH:10]=1)[C:5]([NH2:7])=O>O.CC#N.Cl[Pd]Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH:11]=[O:12])[CH:10]=1)[C:5]#[N:7]

Participants

5

Reactant 1

HCID 866310333-Bromo-5-formylbenzamide

Product 1

HCID 534255233-Bromo-5-formylbenzonitrileYield 40%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalyst2×HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 3-bromo-5-formylbenzamide (1.5 g, 6.58 mmol) in H2O (50.0 mL) and MeCN (50.0 mL) was added PdCl2 (117 mg, 0.658 mmol). The mixture was stirred for 72 h at room temperature and another portion of H2O (100 mL) and MeCN (100 mL) was added followed with addition of PdCl2 (100 mg, 0.56 mol). The mixture was stirred for another 12 hr and concentrated. The residue was dissolved in EtOAc (200 mL), washed with brine (3×50.0 mL), dried over Na2SO4 and concentrated, and then was purified by chromatography (10% EtOAc in hexanes) to give 550 mg of 3-bromo-5-formylbenzonitrile (40%).

Workup

  1. stirringThe mixture was stirred for another 12 hr
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc (200 mL)
  4. washwashed with brine (3×50.0 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customwas purified by chromatography (10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cbc6ae822ead4af3a2d3a9b8609752df
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

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